EP0731685B2 - Emulsion x/o/y multiple stable - Google Patents
Emulsion x/o/y multiple stable Download PDFInfo
- Publication number
- EP0731685B2 EP0731685B2 EP95903303A EP95903303A EP0731685B2 EP 0731685 B2 EP0731685 B2 EP 0731685B2 EP 95903303 A EP95903303 A EP 95903303A EP 95903303 A EP95903303 A EP 95903303A EP 0731685 B2 EP0731685 B2 EP 0731685B2
- Authority
- EP
- European Patent Office
- Prior art keywords
- phase
- emulsion
- stable multiple
- esters
- multiple emulsion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000839 emulsion Substances 0.000 title claims description 93
- 239000012071 phase Substances 0.000 claims description 72
- 239000003995 emulsifying agent Substances 0.000 claims description 42
- 239000003921 oil Substances 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000008346 aqueous phase Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 18
- 239000000499 gel Substances 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 230000007774 longterm Effects 0.000 claims description 5
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002191 fatty alcohols Chemical class 0.000 claims description 4
- 239000004005 microsphere Substances 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical group 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- 229920000223 polyglycerol Chemical class 0.000 claims description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000010696 ester oil Substances 0.000 claims description 2
- 150000002314 glycerols Chemical class 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 235000003441 saturated fatty acids Nutrition 0.000 claims 2
- 150000004671 saturated fatty acids Chemical class 0.000 claims 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- -1 alkyl glucoside esters Chemical class 0.000 claims 1
- 235000013305 food Nutrition 0.000 claims 1
- 229930182478 glucoside Natural products 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000003626 triacylglycerols Chemical class 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 6
- 239000008307 w/o/w-emulsion Substances 0.000 description 6
- 102000008186 Collagen Human genes 0.000 description 5
- 108010035532 Collagen Proteins 0.000 description 5
- 229920001436 collagen Polymers 0.000 description 5
- 239000004408 titanium dioxide Substances 0.000 description 5
- 239000005662 Paraffin oil Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- ANXXYABAFAQBOT-UHFFFAOYSA-N dodecyl-methyl-bis(trimethylsilyloxy)silane Chemical compound CCCCCCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C ANXXYABAFAQBOT-UHFFFAOYSA-N 0.000 description 4
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 3
- 241001295925 Gegenes Species 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229940086555 cyclomethicone Drugs 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000001000 micrograph Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000008365 aqueous carrier Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 229940008099 dimethicone Drugs 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 229940025131 amylases Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
- C11D17/0026—Structured liquid compositions, e.g. liquid crystalline phases or network containing non-Newtonian phase
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/113—Multiple emulsions, e.g. oil-in-water-in-oil
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/54—Silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/90—Liquid crystal material of, or for, colloid system, e.g. g phase
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/924—Significant dispersive or manipulative operation or step in making or stabilizing colloid system
- Y10S516/928—Mixing combined with non-mixing operation or step, successively or simultaneously, e.g. heating, cooling, ph change, ageing, milling
Definitions
- the present application relates to a stable multiple emulsion of the X / O / Y type.
- Stable multiple emulsions of the W / O / W type are known for example from DE-OS 41 31 678 and are described in several literature publications, e.g. A.T. Florence et al., "The Formulation and Stability of Multiple Emulsions", Int. J. Pharmaceutics, Vol.11,277-308,1982.
- EP-A-0 345 075 describes W / O / W type emulsions which contain in the internal aqueous phase an emulsifier having an HLB value not greater than 6, preferably not greater than 5, and in the external aqueous phase Phase contain an emulsifier with an HLB value of at least 8.
- a gelling agent is contained in the internal aqueous phase for adjusting the osmotic pressure and in the external aqueous phase.
- a multiple W / O / W emulsion then consists of a W / O component, i. a water-in-oil emulsion of hydrophilic liquid droplets dispersed in a hydrophobic liquid, and an aqueous component in which this W / O component is dispersed.
- the internal phase of the W / O component may be formed, for example, from an aqueous solution.
- the hydrophobic external phase of the W / O component is usually selected from silicone oil, paraffin oil, triglyceride, fatty alcohol, ester oil or the like, as well as their mixture.
- Such a multiple emulsion can only be prepared with the aid of emulsifiers.
- the emulsifiers are distinguished according to an HLB value by the ratio of their hydrophilic and hydrophobic components; the HLB value results from the percentage of hydrophilic fractions divided by 5 in the total molecular weight of the emulsifier.
- emulsifiers for the formation of W / O emulsions with an HLB value in the range of 3 to 6 emulsifiers as wetting agents with an HLB value in the range of 7 to 9 and emulsifiers for the formation of O / W emulsions with a HLB value in the range of 8 to 18.
- the object of the invention is to provide a simple composite multiple emulsion which can be prepared in a simple manner and is significantly improved in terms of the aforementioned stability criteria and their applicability to the known W / O / W type emulsions.
- the stable multiple emulsion according to the invention should enable the absorption of solids.
- the invention provides a stable multiple emulsion of the X / O / Y type in which X is an oil-immiscible component and O is an oil phase and Y is an aqueous phase and its emulsifier or emulsifiers are selected exclusively from the group W / O emulsifiers, emulsifiers with an HLB value ⁇ 6 and their mixture. It is characterized in that the aqueous phase forms an aqueous gel, wherein the gel is formed by an emulsifier forming a liquid crystalline network and in that the X component is a water-miscible polyol.
- the emulsifier is selected from the group of glycerol esters, sorbitan esters, sorbitol esters, polyglycerol esters, fatty alcohols, propylene glycol esters, alkylglucoside esters, sugar esters, lecithin, silicone copolymers and mixtures or derivatives thereof.
- the emulsions prepared with the aid of at least one of these emulsifiers are obtained by a simple mixing process with stirring, the stability of these multiple emulsions being influenced neither by the incorporated stirring energy nor by the type of stirring tool.
- any commercially available agitator can be used to prepare the multiple emulsion of the present invention.
- the multiple emulsions according to the invention thus produced have high long-term stability and meet the usual stability requirements in the temperature range from -5 ° C to + 45 ° C. Even in the highly diluted with water (1: 100), the multiple emulsions according to the invention are stable: even after aggregation and on frame there is no coalescence, because the creamed material can be completely redispersed by simply shaking, and thus restored Emulsion is then just as stable as the emulsion originally prepared.
- the stable multiple emulsions according to the invention are characterized in particular by the fact that the drops contained therein have a size distribution between 1 .mu.m and 10 .mu.m and thus a relatively small and smaller droplet size than the known multiple emulsions, which is of considerable advantage for many applications.
- an oil phase and a water phase are prepared and heated to a mixing temperature in the range of 20 ° C to 90 ° C, preferably 60 ° C to 80 ° C. Subsequently, the heated oil phase and the heated water phase are zusanmenattention with stirring with a standard agitator; after the addition is stirred for another minute. Subsequently, the emulsion thus obtained is cooled to room temperature or allowed to cool.
- the oil phase contained: sorbitan 6.30% Lauryl methicone copolyol 2.70% paraffin oil 10.00%
- the water phase contained Demineralised water 80.80% Phenonip 0.20%
- this emulsion is referred to as a primary emulsion; she represents a multiple W / O / W emulsion and is used to prepare emulsions with different X / O phases.
- the multiple emulsion was prepared as above; only the composition was different.
- the oil phase contained sorbitan 4.50% Lauryl methicone copolyol 4.50% paraffin oil 10.00% cyclomethicone 10.00%
- the water phase contained Demineralised water 70.80% Phenonip of 0.20%
- This experiment was intended to demonstrate the immiscibility of various X / O phases by microscopic observation, with the corresponding micrographs reproduced below.
- this example also demonstrates that in one phase of the emulsion it is also possible to distribute finely divided solids, such as titanium dioxide, which serve, for example, as light protection filters in cosmetic preparations.
- a secondary emulsion No. 1 consisted of an oil phase and a water phase.
- the oil phase contained Lauryl methicone copolyol 1.5% paraffin oil 16.0% TIOVEIL MOTG (titanium dioxide dispersed in mineral oil / triglyceride) 10.0%; contained the water phase water 71.5% sodium chloride 1.0%: this secondary emulsion forms a W / O emulsion.
- a secondary emulsion No. 2 contained an oil phase and an X component, viz Cyclomethicone + dimethicone copolyol 15% cyclomethicone 30% (Oil phase) and Propylene glycol (X component) 55% and thus forms an X / O emulsion.
- the desired X / O / W emulsion is then obtained by the first of the primary emulsions described above a temperature in the range of 20 ° C to 90 ° C, preferably 50 ° C to 60 ° C, is heated; then, with stirring, the secondary emulsions No. 1 and No. 2 are successively added, and the mixture is cooled to room temperature.
- this primary emulsion and the secondary emulsion no. 1 are combined. After cooling to room temperature, the samples are microscoped; On the micrographs reproduced in the following figures, the droplets of the primary emulsion and the secondary emulsion, which are present separately from one another, can be clearly seen. This structure is retained even after prolonged storage; even after aggregation and creaming and subsequent redispersing, no change is discernible.
- Figure 1 below shows the X / O / Y emulsion in phase contrast at 600x magnification.
- the unstructured droplets of the water phase of secondary emulsion # 1. These unstructured droplets are in the titania-containing oil phase of secondary emulsion # 1.
- Outside the large oil drop are small drops of oil coming from the oil phase of W / O. W primary emulsion are formed; small droplets of water are recognizably distributed in the form of dark dots.
- the two types of oil droplets are clearly separated from each other, and it can be seen that the two oil phases do not mix.
- Figure 2 shows the same microscope image in polarized light. Under these conditions, the unstructured drops of the water phase of the primary emulsion appear dark, while the titanium dioxide particles appear clearly in the oil drop of the secondary emulsion No. 1.
- the small oil droplets outside the large oil crop appear to be less structured and are free of the titanium dioxide particles; they reveal themselves as oil drops of the primary emulsion, in which water drops are indistinctly visible.
- This example is intended to show that the multiple emulsions are present as a gel.
- a liquid-crystalline gel is prepared from a gel-forming emulsifier phase and a water phase.
- the emulsifier phase and the water phase are heated separately to 80 ° C.
- the emulsifier phase is added with stirring into the water phase and the mixture is cooled with further stirring to room temperature.
- the gel phase contained Methylglucosiddistearat 10.0% water 89.8% Phenonip 0.2%
- the liquid-crystalline gel thus obtained is heated to a temperature in the range of 20 ° C to 90 ° C, preferably in the range of 50 ° C to 60 ° C, and mixed successively with the secondary emulsions No. 1 and No. 2 with stirring ,
- the above-mentioned stable multiple emulsions are particularly suitable as carriers for many types of active ingredients because of their stability and because of the stability of the drops present therein, according to the examples the carrier is a liquid-crystalline gel.
- the carrier is a liquid-crystalline gel.
- enzymes such as proteases, lipases and amylases to the detergent. Usually, however, these enzymes are not long-term stable in aqueous solution.
- the preparation of emulsions with various X / O phases also makes it possible to accommodate incompatible active ingredients together in a single carrier.
- incompatible active ingredients such as collagen preparations and urea for application to the skin. This is not possible under normal circumstances when using an aqueous carrier gel. Under these circumstances, namely, the collagen preparation would be denatured in the aqueous phase by urea and thereby lose its effect, cf. H. Lindner "collagen in cosmetics", perfumery and cosmetics Bd. 65, 340-343; 1984.
- this denaturation does not occur. This can be achieved by using an emulsion according to Example 4:
- a carrier gel is prepared on a liquid-crystalline basis; as above, a secondary emulsion No. 1 is obtained by dissolving urea instead of sodium chloride in the water phase and eliminating the titanium dioxide dispersion in the oil phase; according to secondary emulsion no. 2, the collagen preparation is dissolved in the polyol phase and dispersed in the relevant oil phase.
- the carrier gel prepared according to Example 1 then contains the two active ingredients in the separate, not in mutual exchange or in exchange with the aqueous carrier gel oil drops of the various X / O phases, so that the total preparation is long-term.
- the two active ingredients When applied to the skin, although the emulsion is broken, but the two active ingredients are absorbed by the skin in different ways so quickly that it does not come to denaturation of the collagen preparation despite the common application.
- effective drugs can be distributed in different X / O phases at different locations.
- the oil phase and / or the X component may contain solids such as pigments, microspheres, silica gel or wax. Pigments can serve as sunscreen filters (for example in cosmetics), microspheres or silica gel can be used as carriers of active ingredients, and wax is used as the base of, for example, polishes.
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Cosmetics (AREA)
- Colloid Chemistry (AREA)
Claims (15)
- Emulsion multiple stable de type X/O/Y pour laquelle X est un composant non miscible avec de l'huile, O une phase d'huile et Y une phase aqueuse et dont l'émulsifiant ou les émulsifiants sont choisis exclusivement parmi le groupe des émulsifiants d'eau en huile, des émulsifiants ayant une valeur d'équilibre hydrophile/lipophile (HLB) ≤ 6 et de leur mélange, caractérisée en ce que la phase aqueuse forme un gel aqueux, le gel étant formé par un émulsifiant formant un réseau de cristaux liquides et en ce que le composant X est un polyol miscible à l'eau.
- Emulsion multiple stable selon la revendication 1, caractérisée par le fait que l'émulsifiant est choisi parmi le groupe des esters glycériques, des esters de sorbitane, des esters de sorbitol, des esters polyglycériques, des alcools gras, des esters de propylèneglycol, des esters d'alkylglucoside, des esters de sucre, de la lécithine, des copolymères de silicone et de leurs mélanges ou de leurs dérivés.
- Emulsion multiple stable selon la revendication 2, caractérisée par le fait que les esters sont formés d'acides gras saturés à longues chaînes ou d'un mélange consistant à température ambiante d'acides gras non saturés ou saturés à longues chaînes.
- Emulsion multiple stable selon l'une des revendications 1 à 3, caractérisée par le fait que la phase d'huile est choisie parmi le groupe des huiles de silicone, des huiles de paraffine, des triglycérides, des alcools gras, des huiles d'esters ou de leur mélange.
- Emulsion multiple stable selon la revendication 4, caractérisée par le fait que la phase d'huile contient une matière solide choisie parmi le groupe des pigments, des microsphères, du silicagel, de la cire.
- Emulsion multiple stable selon les revendications 1 à 5, caractérisée par le fait que le polyol est choisi parmi le groupe de propylèneglycol, du butylèneglycol, des polyalkylèneglycols, de la glycérine, des polyglycérines ou de leur mélange.
- Emulsion multiple stable selon les revendications 1 à 6, caractérisée par le fait que le composant X comprend une matière active choisie parmi le groupe des matières actives pharmaceutiques, cosmétiques, détergentes, de l'industrie alimentaire ou de l'industrie agricole.
- Emulsion multiple stable selon l'une des revendications 1 à 7, caractérisée par le fait que le composant X comprend une matière solide choisie parmi le groupe des pigments, des microsphères, du gel de silice et de la cire.
- Emulsion multiple stable selon l'une des revendications 1 à 8, caractérisée par le fait que plusieurs composants X sont prévus et qu'ils sont dispersés chaque fois dans une phase d'huile et que les diverses phases X/O ainsi formées sont contenues les unes à côté des autres dans l'émulsion X/O/Y en restant séparées les unes des autres.
- Emulsion multiple stable selon l'une des revendications précédentes, caractérisée par le fait que la phase X/O est formée de gouttes ayant un diamètre situé dans le domaine allant de 1 à 10 µm.
- Procédé destiné à fabriquer de façon simplifiée une émulsion stable multiple de type X/O/Y selon l'une des revendications 1 à 10, caractérisé par le fait qu'une phase X/O fabriquée de façon connue en soi et la phase aqueuse sont réchauffées séparément jusqu'à ce qu'elles atteignent une température située dans le domaine allant de 20°C à 90°C, que la phase X/O réchauffée et la phase aqueuse réchauffée sont unies en les remuant et que le mélange ainsi obtenu est refroidi jusqu'à atteindre la température ambiante.
- Procédé selon la revendication 11, caractérisé par le fait que la phase X/O et la phase aqueuse sont réchauffées séparément jusqu'à ce qu'elles atteignent une température située dans le domaine de 60°C-80°C.
- Procédé selon la revendication 11 ou 12, caractérisé par le fait qu'une première émulsion X/O/Y est réchauffée jusqu'à ce qu'elle atteigne une température située dans le domaine allant de 20°C à 90°C et qu'elle est mélangée en la remuant à une seconde émulsion X/O/Y fabriquée de la même façon et le mélange ainsi obtenu est refroidi jusqu'à atteindre la température ambiante.
- Procédé selon la revendication 13, caractérisé par le fait que la première émulsion X/O/Y est réchauffée jusqu'à ce qu'elle atteigne une température située dans le domaine de 50°C-60°C.
- Utilisation d'au moins un émulsifiant choisi parmi le groupe des émulsifiants d'eau dans l'huile, des émulsifiants ayant une valeur d'équilibre hydrophile/lipophile (HLB) ≤ 6 et de leur mélange, destinée à fabriquer une émulsion X/O/Y multiple et stable à long terme selon l'une des revendications 1 à 10.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4341113 | 1993-12-02 | ||
DE4341113A DE4341113B4 (de) | 1993-12-02 | 1993-12-02 | Stabile multiple X/O/Y-Emulsion |
PCT/EP1994/003955 WO1995015143A2 (fr) | 1993-12-02 | 1994-11-29 | Emulsion x/o/y multiple stable |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0731685A1 EP0731685A1 (fr) | 1996-09-18 |
EP0731685B1 EP0731685B1 (fr) | 2000-07-12 |
EP0731685B2 true EP0731685B2 (fr) | 2007-12-05 |
Family
ID=6504027
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95903303A Expired - Lifetime EP0731685B2 (fr) | 1993-12-02 | 1994-11-29 | Emulsion x/o/y multiple stable |
Country Status (5)
Country | Link |
---|---|
US (1) | US6171600B1 (fr) |
EP (1) | EP0731685B2 (fr) |
AU (1) | AU1241495A (fr) |
DE (2) | DE4341113B4 (fr) |
WO (1) | WO1995015143A2 (fr) |
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US5589177A (en) * | 1994-12-06 | 1996-12-31 | Helene Curtis, Inc. | Rinse-off water-in-oil-in-water compositions |
US5656280A (en) * | 1994-12-06 | 1997-08-12 | Helene Curtis, Inc. | Water-in-oil-in-water compositions |
US6632457B1 (en) * | 1998-08-14 | 2003-10-14 | Incept Llc | Composite hydrogel drug delivery systems |
WO2001080823A2 (fr) | 2000-04-21 | 2001-11-01 | Sol-Gel Technologies Ltd. | Composition a stabilite de preparation accrue et administration d'ingredients actifs topiques |
US7758888B2 (en) * | 2000-04-21 | 2010-07-20 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
US6777450B1 (en) * | 2000-05-26 | 2004-08-17 | Color Access, Inc. | Water-thin emulsions with low emulsifier levels |
EP1289474B1 (fr) * | 2000-05-26 | 2007-05-09 | Color Access, Inc. | Emulsions multiples a emulsifiants faibles |
JP3912965B2 (ja) * | 2000-07-12 | 2007-05-09 | キヤノン株式会社 | 液晶組成物、それを用いた液晶素子および液晶表示装置 |
DE10040969A1 (de) * | 2000-08-22 | 2002-03-07 | Ifac Inst Fuer Angewandte Coll | Verwendung von L-Ascorbinsäure in kosmetischen Emulsionen |
US6936264B2 (en) * | 2001-03-05 | 2005-08-30 | The Procter & Gamble Company | Delivery of reactive agents via multiple emulsions for use in shelf stable products |
DE10211313A1 (de) | 2002-03-14 | 2003-10-02 | Wacker Chemie Gmbh | Mehrfachemulsionen |
DE10211752A1 (de) * | 2002-03-18 | 2003-10-02 | Richter Chem Lab | Aminofunktionelle Polyole enthaltende P/O-Emulsionen |
DE10312763A1 (de) * | 2003-03-21 | 2004-09-30 | IFAC Institut für angewandte Colloidtechnologie GmbH & Co. KG | Verfahren zur Herstellung einer SLN-Dispersion |
GB2400609A (en) * | 2003-04-16 | 2004-10-20 | Reckitt Benckiser | Multiple-emulsion cleaner |
ATE476954T1 (de) | 2003-05-07 | 2010-08-15 | Kemira Pigments Oy | Zusammensetzungen zur gezielten freisetzung von duftstoffen und aromen |
CH715855B1 (de) * | 2003-08-28 | 2020-08-14 | Mibelle Ag | Zubereitung bestehend aus mindestens zwei Nanoemulsionen. |
DE102004002005A1 (de) | 2004-01-14 | 2005-08-11 | Schifferle, René | Portionskapsel mit gemahlenem Kaffee zur Herstellung eines Kaffeegetränks |
WO2006013020A1 (fr) * | 2004-08-04 | 2006-02-09 | Unilever Plc | Composition detergente amelioree comprenant des agents benefiques |
JP5164840B2 (ja) | 2005-08-02 | 2013-03-21 | ソル − ゲル テクノロジーズ リミテッド | 水不溶性成分の金属酸化物被覆 |
MX2009008250A (es) | 2007-02-01 | 2009-08-27 | Sol Gel Technologies Ltd | Composiciones para aplicacion topica que comprenden un peroxido y retinoide. |
EA018275B1 (ru) * | 2007-02-01 | 2013-06-28 | Сол-Джел Текнолоджиз Лтд. | Способ получения частиц, содержащих покрытие из оксида металла, и частицы с покрытием из оксида металла |
NZ580783A (en) * | 2007-06-29 | 2012-04-27 | Nestec Sa | Stable water in oil in water double emulsions comprising two emulsifiers of differing molecular weights |
JP4370365B2 (ja) * | 2007-07-02 | 2009-11-25 | 日清オイリオグループ株式会社 | W/o/w型乳化組成物 |
US9125807B2 (en) | 2007-07-09 | 2015-09-08 | Incept Llc | Adhesive hydrogels for ophthalmic drug delivery |
US8691248B2 (en) | 2008-03-11 | 2014-04-08 | Mary Kay Inc. | Stable three-phased emulsions |
AU2010213612B2 (en) | 2009-02-12 | 2015-04-30 | Incept, Llc | Drug delivery through hydrogel plugs |
US8961501B2 (en) | 2010-09-17 | 2015-02-24 | Incept, Llc | Method for applying flowable hydrogels to a cornea |
US10226417B2 (en) | 2011-09-16 | 2019-03-12 | Peter Jarrett | Drug delivery systems and applications |
US9687465B2 (en) | 2012-11-27 | 2017-06-27 | Sol-Gel Technologies Ltd. | Compositions for the treatment of rosacea |
EP2845959B1 (fr) | 2013-09-04 | 2017-03-01 | Daw Se | Système composite d'isolation thermique avec élément pare-feu ou pare-feu et utilisation d'un tel système pour l'inhibition de la propagation du feu entre étages |
EP3023556B1 (fr) | 2014-11-19 | 2018-02-28 | Daw Se | Élément pare-feu et pare-feu constitué d'éléments pare-feu |
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US3702302A (en) * | 1970-05-28 | 1972-11-07 | Vernon Columbus Wilson | True self-heating composition |
GB1541463A (en) * | 1975-10-11 | 1979-02-28 | Lion Dentifrice Co Ltd | Process for prparing a multiple emulsion having a dispersing form of water-phase/oil-phase/water-phase |
ATA207181A (de) * | 1981-05-08 | 1983-09-15 | Schering Wien | Kosmetisches mittel und verfahren zu seiner herstellung |
EP0120967B1 (fr) * | 1982-10-01 | 1987-06-03 | Meiji Milk Products Company Limited | Procede de production de compositions alimentaires d'huile et de graisse a emulsion eau/huile/eau |
JPS59127646A (ja) * | 1982-12-24 | 1984-07-23 | Kobayashi Kooc:Kk | W/o/w型エマルジヨンの製造方法 |
US4626443A (en) * | 1984-03-02 | 1986-12-02 | Meiji Milk Products Company Limited | Process for preparing dressings comprising W/O/W type multiple emulsions |
JPS60183031A (ja) * | 1984-03-02 | 1985-09-18 | Meiji Milk Prod Co Ltd | W/o/w型複合エマルジヨンの製造法 |
US4626444A (en) * | 1984-03-02 | 1986-12-02 | Meiji Milk Products Company Limited | Process for preparation of dressings comprising W/O/W type multiple emulsions |
JPS60199833A (ja) * | 1984-03-26 | 1985-10-09 | Meiji Milk Prod Co Ltd | 医薬品、化粧品等用w/o/w型複合エマルジヨンの製造法 |
US5143722B1 (en) * | 1986-12-19 | 1999-08-24 | Revlon Consumer Prod Corp | Cosmetic makeup compositions comprising water-in-oil emulsions containing pigment |
GB8813161D0 (en) * | 1988-06-03 | 1988-07-06 | Unilever Plc | Emulsions |
US5061688A (en) * | 1988-08-19 | 1991-10-29 | Illinois Institute Of Technology | Hemoglobin multiple emulsion |
DE3922079C2 (de) * | 1989-07-05 | 1996-06-13 | Hanse Chemie Gmbh | Polysiloxandispersion, Verfahren zu ihrer Herstellung und ihre Verwendung |
GB9005384D0 (en) * | 1990-03-09 | 1990-05-02 | Boots Co Plc | Cosmetic formulation |
DE4131678A1 (de) | 1991-04-13 | 1992-10-15 | Beiersdorf Ag | Stabile multiple emulsionen |
DE4136699A1 (de) * | 1991-11-07 | 1992-10-22 | Lancaster Group Ag | Verfahren zur herstellung von stabilen, komplexen emulsionssystemen des typs wasser-oel-wasser und deren verwendung als kosmetische praeparate |
US5304334A (en) * | 1992-04-28 | 1994-04-19 | Estee Lauder, Inc. | Method of preparing a multiphase composition |
US5304370A (en) * | 1992-06-09 | 1994-04-19 | Revlon Consumer Products Corporation | Hair relaxer composition and associated methods |
FR2693466B1 (fr) * | 1992-07-09 | 1994-09-16 | Oreal | Composition cosmétique sous forme d'émulsion triple eau/huile de silicone/eau gélifiée. |
FR2702391B1 (fr) * | 1993-03-11 | 1995-04-28 | Roussel Uclaf | Nouvelles émulsions multiples, leur préparation, leur application à la préparation de compositions cosmétiques et ces compositions cosmétiques. |
-
1993
- 1993-12-02 DE DE4341113A patent/DE4341113B4/de not_active Expired - Fee Related
-
1994
- 1994-11-29 AU AU12414/95A patent/AU1241495A/en not_active Abandoned
- 1994-11-29 US US08/652,531 patent/US6171600B1/en not_active Expired - Fee Related
- 1994-11-29 WO PCT/EP1994/003955 patent/WO1995015143A2/fr active IP Right Grant
- 1994-11-29 EP EP95903303A patent/EP0731685B2/fr not_active Expired - Lifetime
- 1994-11-29 DE DE59409446T patent/DE59409446D1/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0731685B1 (fr) | 2000-07-12 |
US6171600B1 (en) | 2001-01-09 |
WO1995015143A3 (fr) | 1995-07-13 |
DE4341113B4 (de) | 2006-04-13 |
DE59409446D1 (de) | 2000-08-17 |
AU1241495A (en) | 1995-06-19 |
WO1995015143A2 (fr) | 1995-06-08 |
EP0731685A1 (fr) | 1996-09-18 |
DE4341113A1 (de) | 1995-06-08 |
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